JP2007524239A5 - - Google Patents
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- JP2007524239A5 JP2007524239A5 JP2006551605A JP2006551605A JP2007524239A5 JP 2007524239 A5 JP2007524239 A5 JP 2007524239A5 JP 2006551605 A JP2006551605 A JP 2006551605A JP 2006551605 A JP2006551605 A JP 2006551605A JP 2007524239 A5 JP2007524239 A5 JP 2007524239A5
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- Prior art keywords
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- Prior art date
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- 239000003446 ligand Substances 0.000 claims description 32
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 16
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 8
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000007944 thiolates Chemical class 0.000 claims description 2
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 0 CN(C)c1ccnc(-c(cc(*)c(F)c2*)c2F)c1 Chemical compound CN(C)c1ccnc(-c(cc(*)c(F)c2*)c2F)c1 0.000 description 1
- JAPZEBUITZWKCW-UHFFFAOYSA-N CN(C)c1ccnc(-c(cc(C(F)(F)F)c(F)c2C(F)(F)F)c2F)c1 Chemical compound CN(C)c1ccnc(-c(cc(C(F)(F)F)c(F)c2C(F)(F)F)c2F)c1 JAPZEBUITZWKCW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical compound PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76829804A | 2004-01-30 | 2004-01-30 | |
| US10/768,298 | 2004-01-30 | ||
| US10/774,286 | 2004-02-06 | ||
| US10/774,286 US7476452B2 (en) | 2000-06-30 | 2004-02-06 | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| PCT/US2005/003338 WO2005075597A2 (en) | 2004-01-30 | 2005-01-28 | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007524239A JP2007524239A (ja) | 2007-08-23 |
| JP2007524239A5 true JP2007524239A5 (enExample) | 2008-03-13 |
| JP4918365B2 JP4918365B2 (ja) | 2012-04-18 |
Family
ID=34841270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551605A Expired - Lifetime JP4918365B2 (ja) | 2004-01-30 | 2005-01-28 | フッ素化フェニルピリジン配位子を有するエレクトロルミネセンスイリジウム化合物、およびかかる化合物で製造されたデバイス |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7476452B2 (enExample) |
| JP (1) | JP4918365B2 (enExample) |
| TW (1) | TWI363792B (enExample) |
| WO (1) | WO2005075597A2 (enExample) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7476452B2 (en) * | 2000-06-30 | 2009-01-13 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| US7816016B1 (en) | 2003-02-13 | 2010-10-19 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds and devices made therefrom |
| SE528408C2 (sv) | 2005-03-07 | 2006-11-07 | Interactive Inst Ii Ab | En metod och en anordning för visuell indikering av ström- eller effektförbrukning i en elkabel |
| WO2007004113A2 (en) | 2005-06-30 | 2007-01-11 | Koninklijke Philips Electronics N.V. | Electro luminescent metal complexes |
| JP2007059783A (ja) * | 2005-08-26 | 2007-03-08 | Showa Denko Kk | 有機ｅｌ素子、その製造方法およびその用途 |
| US8115378B2 (en) * | 2006-12-28 | 2012-02-14 | E. I. Du Pont De Nemours And Company | Tetra-substituted chrysenes for luminescent applications |
| US8257836B2 (en) | 2006-12-29 | 2012-09-04 | E I Du Pont De Nemours And Company | Di-substituted pyrenes for luminescent applications |
| CN105669765A (zh) | 2007-05-18 | 2016-06-15 | 株式会社半导体能源研究所 | 有机金属配合物，包含该有机金属配合物的组合物和发光元件 |
| CN101679207B (zh) | 2007-06-01 | 2014-05-28 | E.I.内穆尔杜邦公司 | 用于深蓝色发光应用的* |
| JP5401449B2 (ja) * | 2007-06-01 | 2014-01-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 緑色発光用途のためのクリセン類 |
| ATE536340T1 (de) * | 2007-06-01 | 2011-12-15 | Du Pont | Blaue lumineszente materialien |
| CN101918512B (zh) | 2007-06-01 | 2014-09-24 | E.I.内穆尔杜邦公司 | 绿色发光材料 |
| TW200911821A (en) * | 2007-06-08 | 2009-03-16 | Solvay | Light emitting material |
| US8192848B2 (en) * | 2008-01-11 | 2012-06-05 | E I Du Pont De Nemours And Company | Substituted pyrenes and associated production methods for luminescent applications |
| JP5609022B2 (ja) * | 2008-06-23 | 2014-10-22 | 住友化学株式会社 | 金属錯体の残基を含む高分子化合物及びそれを用いた素子 |
| EP2294641A4 (en) | 2008-06-26 | 2012-08-08 | Du Pont | OLED LIGHTING |
| WO2009158558A2 (en) * | 2008-06-26 | 2009-12-30 | E. I. Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| JP5687628B2 (ja) * | 2008-11-19 | 2015-03-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 青色または緑色ルミネセンス用途のクリセン化合物 |
| US8932733B2 (en) * | 2008-12-19 | 2015-01-13 | E I Du Pont De Nemours And Company | Chrysene derivative host materials |
| US8263973B2 (en) * | 2008-12-19 | 2012-09-11 | E I Du Pont De Nemours And Company | Anthracene compounds for luminescent applications |
| US8531100B2 (en) | 2008-12-22 | 2013-09-10 | E I Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
| KR20110114594A (ko) * | 2008-12-22 | 2011-10-19 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 광활성 조성물 및 그 조성물로 제조된 전자 소자 |
| WO2010090362A1 (en) * | 2009-02-06 | 2010-08-12 | Pusan National University Industry-University Cooperation Foundation | Phosphorescent light-emitting iridium complex containing pyridyltriazole ligand |
| US8759818B2 (en) * | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| WO2010114583A1 (en) | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
| EP2669351A1 (en) | 2009-05-19 | 2013-12-04 | E. I. du Pont de Nemours and Company | Chrysene compounds for luminescent applications |
| JP2012532111A (ja) | 2009-07-01 | 2012-12-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ルミネセンス用途のクリセン化合物 |
| TW201105615A (en) * | 2009-08-13 | 2011-02-16 | Du Pont | Chrysene derivative materials |
| TW201117651A (en) * | 2009-08-24 | 2011-05-16 | Du Pont | Organic light-emitting diode luminaires |
| US8471247B2 (en) * | 2009-08-24 | 2013-06-25 | E I Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| CN102484214A (zh) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | 有机发光二极管灯具 |
| CN102484215A (zh) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | 有机发光二极管灯具 |
| KR20120066027A (ko) * | 2009-08-24 | 2012-06-21 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기 발광 다이오드 조명기구 |
| JP5726877B2 (ja) * | 2009-08-24 | 2015-06-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 有機発光ダイオード照明器具 |
| KR20120091144A (ko) | 2009-09-29 | 2012-08-17 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 발광 응용을 위한 중수소화된 화합물 |
| CN102596893A (zh) | 2009-10-19 | 2012-07-18 | E.I.内穆尔杜邦公司 | 用于电子应用的三芳基胺化合物 |
| KR101782660B1 (ko) | 2009-10-19 | 2017-09-27 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전자적 응용을 위한 트라이아릴아민 화합물 |
| US8716699B2 (en) * | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| EP2493887A4 (en) | 2009-10-29 | 2013-06-19 | Du Pont | DETERERATED COMPOUNDS FOR ELECTRONIC APPLICATIONS |
| US8674343B2 (en) | 2009-10-29 | 2014-03-18 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US8716700B2 (en) | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| EP2510071A4 (en) * | 2009-12-09 | 2013-12-18 | Du Pont | DEUTERIZED CONNECTION AS PART OF A CONNECTION COMBINATION FOR ELECTRICAL APPLICATIONS |
| US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
| US8465849B2 (en) * | 2009-12-21 | 2013-06-18 | E I Du Pont De Nemours And Company | Deuterated zirconium compound for electronic applications |
| JP2013540699A (ja) | 2010-08-11 | 2013-11-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性化合物および組成物、ならびにその組成物を用いて作製した電子デバイス |
| EP2609640B1 (en) | 2010-08-24 | 2015-11-25 | E. I. du Pont de Nemours and Company | Photoactive composition and electronic device made with the composition |
| CN102408448B (zh) * | 2010-09-21 | 2015-04-15 | 中国科学院福建物质结构研究所 | 一种检测次氯酸根的磷光材料 |
| TW201229010A (en) | 2010-12-13 | 2012-07-16 | Du Pont | Electroactive materials |
| US9269909B2 (en) | 2010-12-15 | 2016-02-23 | E I Du Pont De Nemours And Company | Electroactive material and devices made with such materials |
| TW201229003A (en) | 2010-12-17 | 2012-07-16 | Du Pont | Anthracene derivative compounds for electronic applications |
| US20130248843A1 (en) | 2010-12-17 | 2013-09-26 | E I Du Pont De Nemours And Company | Anthracene derivative compounds for electronic applications |
| TW201229204A (en) | 2010-12-17 | 2012-07-16 | Du Pont | Anthracene derivative compounds for electronic applications |
| EP2655547A1 (en) | 2010-12-20 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Compositions for electronic applications |
| WO2012087960A1 (en) | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Triazine derivatives for electronic applications |
| US20130264561A1 (en) | 2010-12-20 | 2013-10-10 | E I Du Pont De Nemours And Company | Electroactive compositions for electronic applications |
| CN103261172B (zh) | 2010-12-21 | 2016-05-04 | E.I.内穆尔杜邦公司 | 包括嘧啶化合物的电子装置 |
| KR20140075012A (ko) | 2011-10-19 | 2014-06-18 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 조명용 유기 전자 소자 |
| JP2012039161A (ja) * | 2011-11-22 | 2012-02-23 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| EP2828273B1 (en) * | 2012-03-23 | 2019-02-20 | E. I. du Pont de Nemours and Company | Green luminescent materials |
| JP2014529897A (ja) * | 2012-04-30 | 2014-11-13 | ヨル チョン ケミカル カンパニーリミテッドＹｏｕｌ Ｃｈｏｎ Ｃｈｅｍｉｃａｌ Ｃｏ．， Ｌｔｄ． | 新規な金属錯化合物及びそれを含む青色燐光有機発光素子 |
| KR102065586B1 (ko) | 2013-01-30 | 2020-01-14 | 삼성디스플레이 주식회사 | 유기금속 착체 및 이를 포함한 유기 발광 소자 |
| KR102037375B1 (ko) | 2013-02-13 | 2019-10-29 | 삼성디스플레이 주식회사 | 유기금속 착체 및 이를 포함한 유기 발광 소자 |
| US9748497B2 (en) | 2013-02-25 | 2017-08-29 | E I Du Pont De Nemours And Company | Electronic device including a diazachrysene derivative |
| US10134988B2 (en) | 2013-12-13 | 2018-11-20 | E I Du Pont De Nemours And Company | System for forming an electroactive layer |
| US9944846B2 (en) | 2014-08-28 | 2018-04-17 | E I Du Pont De Nemours And Company | Compositions for electronic applications |
| US9972783B2 (en) | 2015-03-25 | 2018-05-15 | E I Du Pont De Nemours And Company | High energy triarylamine compounds for hole transport materials |
| US10804473B2 (en) | 2015-05-21 | 2020-10-13 | Lg Chem, Ltd. | Electron transport materials for electronic applications |
| US9966542B2 (en) | 2016-06-02 | 2018-05-08 | E I Du Pont De Nemours And Company | Electroactive materials |
| RU2657496C1 (ru) * | 2017-07-10 | 2018-06-14 | Сиа Эволед | Разнолигандные фторзамещенные ароматические карбоксилаты лантанидов, проявляющие люминесцентные свойства, и органические светодиоды на их основе |
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| WO1996003410A1 (de) | 1994-07-25 | 1996-02-08 | Boehringer Mannheim Gmbh | Hydrophile metallkomplexe |
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| BRPI0009215B1 (pt) | 1999-03-23 | 2017-05-09 | Univ Southern California | complexos metálicos ciclometalizados como dopantes fosforescentes em diodos emissores de luz orgânicos |
| EP1729327B2 (en) | 1999-05-13 | 2022-08-10 | The Trustees Of Princeton University | Use of a phosphorescent iridium compound as emissive molecule in an organic light emitting device |
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| JP4048521B2 (ja) * | 2000-05-02 | 2008-02-20 | 富士フイルム株式会社 | 発光素子 |
| US7476452B2 (en) * | 2000-06-30 | 2009-01-13 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| US6670645B2 (en) * | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
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| US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| EP2566302B1 (en) | 2000-08-11 | 2015-12-16 | The Trustees of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorence |
| JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
| JP4343528B2 (ja) | 2000-11-30 | 2009-10-14 | キヤノン株式会社 | 発光素子及び表示装置 |
| JP4006335B2 (ja) * | 2000-11-30 | 2007-11-14 | キヤノン株式会社 | 発光素子及び表示装置 |
| JP3812730B2 (ja) * | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| US7320833B2 (en) * | 2001-11-07 | 2008-01-22 | E.I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| EP2306788A1 (en) | 2001-12-26 | 2011-04-06 | E. I. du Pont de Nemours and Company | Iridium compounds and devices made therewith |
| US6869695B2 (en) * | 2001-12-28 | 2005-03-22 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
| US6919139B2 (en) * | 2002-02-14 | 2005-07-19 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with phosphinoalkoxides and phenylpyridines or phenylpyrimidines and devices made with such compounds |
| DE10215010A1 (de) | 2002-04-05 | 2003-10-23 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| CN100340630C (zh) * | 2002-08-16 | 2007-10-03 | 南加利福尼亚大学 | 有机发光材料和器件 |
| US6916554B2 (en) * | 2002-11-06 | 2005-07-12 | The University Of Southern California | Organic light emitting materials and devices |
| CN1703937B (zh) * | 2002-10-09 | 2010-11-24 | 出光兴产株式会社 | 有机电致发光的器件 |
| KR100682858B1 (ko) * | 2003-06-26 | 2007-02-15 | 삼성에스디아이 주식회사 | 유기 금속 착물 및 이를 채용한 유기 전계 발광 소자 |
| US7198730B2 (en) * | 2003-08-28 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Phosphorescent material |
| JP4438394B2 (ja) * | 2003-10-30 | 2010-03-24 | 三菱化学株式会社 | 有機金属錯体およびそれを用いた有機電界発光素子 |
-
2004
- 2004-02-06 US US10/774,286 patent/US7476452B2/en not_active Expired - Fee Related
-
2005
- 2005-01-28 WO PCT/US2005/003338 patent/WO2005075597A2/en not_active Ceased
- 2005-01-28 TW TW094102739A patent/TWI363792B/zh not_active IP Right Cessation
- 2005-01-28 JP JP2006551605A patent/JP4918365B2/ja not_active Expired - Lifetime
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